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Unwinding of supercoiled Col E1-DNA after covalent binding of the ultimate carcinogen N-acetoxy-N-2-acetylaminofluorene and its 7-iodo derivative.

作者信息

Lang M C, Freund A M, de Murcia G, Fuchs R P, Daune M P

出版信息

Chem Biol Interact. 1979 Dec;28(2-3):171-80. doi: 10.1016/0009-2797(79)90159-5.

DOI:10.1016/0009-2797(79)90159-5
PMID:549740
Abstract

The unwinding of superhelical Col E1-DNA was studied by means of gel electrophoresis and electron microscopy after covalent binding of N-acetoxy-N-2-[14C]acetylaminofluorene (N-Aco-[14C]AAF) and its 7-iodo derivative (N-Aco-[14C]AAIF). Studies with both compounds indicated that complete unwinding of the supercoiled DNA required the binding of hydrocarbon residue to about 3% of the bases. Thus the unwinding angle per residue of N-2-acetylaminofluorene (AAF) and its 7-iodo derivative was of 22 degrees +/- 3 and 18 degrees +/- 3 respectively. Our results are in good agreement with those obtained by Drinkwater et al. [9]. Precedent studies from this laboratory have shown that N-Aco-AAF and its 7-iodo derivative induce different local conformation change in native DNA (insertion-denaturation model and outside binding model respectively). The unexpected ability of the 7-iodo derivative to unwind supercoiled DNA is discussed.

摘要

相似文献

1
Unwinding of supercoiled Col E1-DNA after covalent binding of the ultimate carcinogen N-acetoxy-N-2-acetylaminofluorene and its 7-iodo derivative.
Chem Biol Interact. 1979 Dec;28(2-3):171-80. doi: 10.1016/0009-2797(79)90159-5.
2
Analysis at the sequence level of mutations induced by the ultimate carcinogen N-acetoxy-N-2-acetylaminofluorene.对终极致癌物N-乙酰氧基-N-2-乙酰氨基芴诱导的突变进行序列水平分析。
Environ Health Perspect. 1983 Mar;49:135-40. doi: 10.1289/ehp.8349135.
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Modification of PM2 DNA with N-acetoxy-2-acetylaminofluorene: changes in buoyant density, electrophoretic mobility and electron microscopic structure.用N-乙酰氧基-2-乙酰氨基芴修饰PM2 DNA:浮力密度、电泳迁移率和电子显微镜结构的变化
Cancer Lett. 1980 Feb;8(4):343-51. doi: 10.1016/0304-3835(80)90151-2.
4
Comparative orientation of the fluorene residue in native DNA modified by N-acetoxy-N-2-acetylaminofluorene and two 7-halogeno derivatives.N-乙酰氧基-N-2-乙酰氨基芴及其两种7-卤代衍生物修饰的天然DNA中芴残基的比较取向
Biochemistry. 1976 Jul 27;15(15):3347-51. doi: 10.1021/bi00660a027.
5
An ultimate chemical carcinogen, N-acetoxy-2-acetylaminofluorene, detects non-B DNA structures that are reactive with chloroacetaldehyde in supercoiled plasmid DNA.一种终极化学致癌物,N-乙酰氧基-2-乙酰氨基芴,可检测超螺旋质粒DNA中与氯乙醛反应的非B型DNA结构。
Carcinogenesis. 1988 Mar;9(3):457-61. doi: 10.1093/carcin/9.3.457.
6
Spectroscopic study of the effects of C-alkylation of N-acetoxy-N-acetyl-2-aminofluorene on some properties of the carcinogen-modified DNA.N-乙酰氧基-N-乙酰基-2-氨基芴的C-烷基化对致癌物修饰DNA某些性质影响的光谱研究
Cancer Biochem Biophys. 1983;6(4):261-7.
7
Interaction of the synthetic ultimate carcinogens, N-sulfonoxy- and N-acetoxy-2-acetylaminofluorene, and of enzymatically activated N-hydroxy-2-acetylaminofluorene with nucleophiles.合成终极致癌物N-磺酰氧基-和N-乙酰氧基-2-乙酰氨基芴,以及酶促活化的N-羟基-2-乙酰氨基芴与亲核试剂的相互作用。
Carcinogenesis. 1986 Mar;7(3):405-11. doi: 10.1093/carcin/7.3.405.
8
C-alkylation of N-acetoxy-N-2-acetylaminofluorene: effects on its reaction with DNA in vitro.N-乙酰氧基-N-2-乙酰氨基芴的C-烷基化:对其体外与DNA反应的影响
Cancer Biochem Biophys. 1984 Jun;7(2):89-99.
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Effect of pH on the ratio of substitution products in DNA after reaction with the carcinogen N-acetoxy-2-acetylaminofluorene.pH对致癌物N-乙酰氧基-2-乙酰氨基芴与DNA反应后取代产物比例的影响。
Cancer Lett. 1979 Jul;7(2-3):141-6. doi: 10.1016/s0304-3835(79)80109-3.
10
Comparative studies on the 7-iodo and 7-fluoro derivatives of N-acetoxy-N-2-acetylaminofluorene: binding sites on DNA and conformational change of modified deoxytrinucleotides.N-乙酰氧基-N-2-乙酰氨基芴的7-碘和7-氟衍生物的比较研究:DNA上的结合位点及修饰的脱氧三核苷酸的构象变化
Biochemistry. 1978 Jun 27;17(13):2561-7. doi: 10.1021/bi00606a016.

引用本文的文献

1
Comparison of the reactivity of B-DNA and Z-DNA with two isosteric chemical carcinogens: 2-N,N-acetoxyacetylaminofluorene and 3-N,N-acetoxyacetylamino-4,6-dimethyldipyrido-[1,2-a:3',2' -d] imidazole.B-DNA和Z-DNA与两种等排化学致癌物的反应性比较:2-N,N-乙酰氧基乙酰氨基芴和3-N,N-乙酰氧基乙酰氨基-4,6-二甲基二吡啶并-[1,2-a:3',2'-d]咪唑。
Nucleic Acids Res. 1987 Jul 24;15(14):5629-42. doi: 10.1093/nar/15.14.5629.
2
Differences in unwinding of supercoiled DNA induced by the two enantiomers of anti-benzo[a]pyrene diol epoxide.反式苯并[a]芘二醇环氧化物的两种对映体诱导的超螺旋DNA解旋差异。
Nucleic Acids Res. 1992 Dec 11;20(23):6167-76. doi: 10.1093/nar/20.23.6167.